N-bromobutanimide → Benzyl 2-bromo-3-oxobutanoate

Participants

Reaction Steps

To a stirring dispersion of benzyl acetoacetate (20 ml, 116 mmol) and NBS (21.64 g, 122 mmol) in Et2O (1000 ml) was added ammonium acetate (0.893 g, 11.58 mmol). The reaction was stirred at RT for 4 hours and then filtered, washed with water (400 ml), brine, dried over MgSO4 and concentrated in vacuo to give the title compound as a yellow oil; 1H NMR (400 MHz, CDCl3) δ 7.37-7.42 (5H, m, 5×ArH), 5.27 (2H, s, ArCH2OR), 4.82 (1H, s, CHBr), 2.42 (3H, s, RCOCH3).

Provenance & Evidence